It’s easy to think that a lot of people would state that Chewbacca would simply, and literally, rip Bossk limb from limb since according to Han Solo, Wookies are known to do this. But the thing is that Chewbacca isn’t quite the same as other members of his kind, and his ability to escape is sometimes superior to his ability to fight up close and personal. The fact that Bossk is one of the most vicious Trandoshans in the Star Wars universe, and discounting him as just another being that has an ancestral issue with another species is way too dismissive. Bossk didn’t become a bounty hunter for fun, after all, he decided to hunt sentient beings for a living because he’s good at it. The Trandoshan is one of the most efficient hunters in the galaxy, but his downfall is that when enraged he ends up expending a great deal of energy and he becomes extremely unlucky at times, which is likely why many people think of him as just another villain that is constantly outdone by those he goes up against that are capable of fighting back.
This fight would be interesting since both combatants are incredibly strong, they both have teeth and claws that can do damage, and they carry weapons that pack a heavy punch. Where it might start to break down however is when it comes to which environment the two are fighting in, and whether or not there are any means of escape. From a distance, it’s been stated that Chewbacca has a slight advantage since while Bossk is a great shot and an expert hunter, Chewie’s bowcaster is equally powerful, and his aim is great enough to take a stormtrooper off a speeder bike, which moves much faster than Bossk can. Where Bossk’s real strength might lie is in a fight that gets up close and personal since his strength is impressive enough to keep up with Chewie.
Where it comes down to a victory by Chewbacca though is the fact that he can become enraged as well and exercise great feats of strength, and this is where things become dangerous for Bossk. It’s true that Trandoshans can regenerate limbs, and that they do have a healing factor, but it’s also fair to note that it doesn’t happen immediately, and their limbs don’t grow back that quickly. This means that ripping off one limb and beating Bossk down with it is possible for Chewie, and ripping off more than one limb would likely be the plan so that Chewie could make his getaway, or maybe deal with Bossk for good. Given that Chewbacca isn’t a murderer and does have a great deal of honor it’s not likely that he would kill the Trandoshan, but would probably disarm him, literally, so that his enemy couldn’t come after him right away. This fight could easily go on for a while since Chewie doesn’t have the lack of inhibitions that Bossk does, but a hand to hand battle could get bloody since discounting Bossk’s teeth and claws is a mistake, but thinking that Chewbacca can’t fight would be another mistake, and a very costly one.
The Trandoshans are quite nasty since they’re known to be killers quite often even if a good number of them are merchants and have taken on other appearances in the Star Wars universe. The fact is that they look menacing and more than a little evil, but Bossk is by far one of the most aggressive members of the species. Chewbacca is definitely aggressive, but as far as being a warrior, those days were back in the Clone Wars and since that time he became a smuggler, a mechanic, and is more or less a bodyguard and friend to Han Solo up until his death. But this doesn’t mean that Chewie is any less aggressive when he needs to be. The big Wookie is still every bit as deadly as he used to be, but the act of getting away is a far stronger instinct a lot of times since Chewie isn’t stupid, he knows when to stand and fight and he knows when to strike back and run away. With Bossk, it’s either disarm him and run, or stay and fight, and possibly meet his end.
Chewie is the kind of character that has evolved throughout his time in the Star Wars franchise, while Bossk has kind of remained the same. Both of them are tough, resourceful, and more than a little skilled when it comes to a fight. But pitting them against each other is akin to setting a dog and cat against one another, they’re bound to go after each other tooth and nail, quite literally, and it’s usually assumed that the most aggressive of the two will end up walking away. If pushed to that degree, Chewbacca would emerge the victor.
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